Thiophosgene → HCID 88157933, compound

Participants

Reaction Steps

20.8 ml of sodium hydrogencarbonate and 0.05 ml of thiophosgen were added to a solution of 50.2 mg of 4-(benzothiazol-2-ylmethoxy)aniline [prepared as described in Example 3 (b)] in 2 ml of methylene chloride and the resulting mixture was stirred at room temperature for 2 hours. 8 ml of methylene chloride were then added to the reaction mixture and the resulting mixture was washed with water and the organic fraction then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was then dissolved in 3 ml of tetrahydrofuran and 0.01 ml of methanol. 13.2 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to the resulting mixture which was then stirred at room temperature for 30 minutes. At the end of this time, 5 mg of sodium methoxide were added to the reaction mixture which was then stirred for 30 minutes. A saturated aqueous sodium chloride solution was then added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was recrystallized from a mixed solvent of ethyl acetate and hexane to give 49.7 mg (yield 76%) of the title compound as a solid having a melting point of 160°-162° C.

Provenance & Evidence